Ethanol → HCID 178475132, compound

HRID 441977Notes

Reaction equation

HRID 441977 reaction equation
C[N:2]([N:22]=O)[C:3]1[CH2:14][N+:13]([O-:15])=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=2[N:4]=1.[CH2:24]([OH:26])[CH3:25]>C(N(CC)CC)C>[C:24]([NH:22][NH:2][C:3]1[CH2:14][N+:13]([O-:15])=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=2[N:4]=1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 702EthanolHCID 40094N-Nitrosochlordiazepoxide

Product 1

HCID 178475132HCID 178475132, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 3.3 g. of N-nitrosochlordiazepoxide, 30 ml. of ethanol, 3 ml. of triethylamine and 2 g. of acetyl hydrazide was refluxed for 24 hours. The solvent was removed and replaced by n-butanol. After additional 24 hours of reflux, the reaction mixture was evaporated. The residue was slurried with methylene chloride. The insoluble material was collected and recrystallized from methylene chloride/ethanol to yield 2-(2-acetylhydrazino)-7-chloro-5-phenyl-3H-1,4-benzodiazepine 4-oxide. The methylene chloride soluble part was chromatographed over 70 g. of silica gel using 10 percent ethanol in methylene chloride. Crystallization of the clean fractions from ethyl acetate yielded 8-chloro-1-methyl-6-phenyl-4H-s-triazolo[4,5-a][1,4]benzodiazepine 5-oxide with a melting point of 278°-282°.

Workup

  1. additionA mixture of 3.3 g
  2. customThe solvent was removed
  3. temperatureAfter additional 24 hours of reflux
  4. customthe reaction mixture was evaporated
  5. customThe insoluble material was collected
  6. customrecrystallized from methylene chloride/ethanol

Sources & evidence

ORD record
ord-c32de36416854f30873942f210d105d9
Source dataset
uspto-grants-1977_08
Patent number
US04044016

Reaction notes

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